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Sigma-Aldrich

Tributyl(1-ethoxyvinyl)tin

97%

Synonym(s):

(1-Ethoxyvinyl)tri-n-butylstannane

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1 G
€29.40
5 G
€140.00
25 G
€650.00
100 G
€1,274.00

About This Item

Linear Formula:
[CH3(CH2)3]3SnC(OC2H5)=CH2
CAS Number:
97674-02-7
Molecular Weight:
361.15
MDL number:
MFCD00010240
UNSPSC Code:
12352103
PubChem Substance ID:
24856628
NACRES:
NA.22

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Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.476 (lit.)

bp

85-86 °C/0.1 mmHg (lit.)

density

1.069 g/mL at 25 °C (lit.)

SMILES string

CCCC[Sn](CCCC)(CCCC)C(=C)OCC

InChI

1S/C4H7O.3C4H9.Sn/c1-3-5-4-2;3*1-3-4-2;/h1,4H2,2H3;3*1,3-4H2,2H3;

InChI key

HGXJOXHYPGNVNK-UHFFFAOYSA-N

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General description

This vinylstannane undergoes Stille coupling with a vinyl triflate, giving, after hydrolysis, an α,β−unsaturated ketone, thus acting as an acetyl anion equivalent.[1]

Application

Electrophilic methyl ketone equivalent used in a recent synthesis of a 13-oxophorbine (chlorophyll) from the corresponding 13-bromochlorin.[2]
Reagent employed in palladium-catalyzed coupling reactions with sulfoxides,[3] α-haloethers,[4] and chlorocyclobutenones.[5] Also used to convert acid chlorides to α-oxygenated enones.[6]

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT RE 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP5674
SHBG1597V
SHBC6956V
04096EMV
16096EMV

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Journal of the American Chemical Society, 114, 1412-1412 (1992)
Younggi Choi et al.
The Journal of organic chemistry, 69(11), 3758-3764 (2004-05-22)
2-Azabicyclo[2.2.2]oct-5-enes bearing an endo alkenyl substituent were synthesized by Diels-Alder addition of methyl vinyl ketone to a 1,6-dihydropyridine derived from methyl nicotinate. Although 1,5-dienes with this skeleton were unreactive under thermal conditions, they were photochemically reactive. Irradiation of these dienes
Joydev K Laha et al.
The Journal of organic chemistry, 71(18), 7049-7052 (2006-08-26)
A new route to 13(1)-oxophorbines, the parent macrocycle of chlorophylls, begins with the synthesis of a 13-bromochlorin. Pd-mediated coupling of the latter with tributyl(1-ethoxyvinyl)tin and subsequent acidic hydrolysis afforded the 13-acetylchlorin (1). Treatment of 1 with NBS afforded the 15-bromo
Tetrahedron Letters, 34, 2429-2429 (1993)
Tetrahedron Letters, 33, 4885-4885 (1992)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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